Lopinavir

Lopinavir

Systematic (IUPAC) name
(2S)-N-[(2S,4S,5S)-5-[2-(2,6-dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a602015
Pregnancy cat.	C (US)
Legal status	POM (UK) ℞-only (US)
Routes	Oral
Pharmacokinetic data
Bioavailability	Unknown
Protein binding	98-99%
Metabolism	Hepatic
Half-life	5 to 6 hours
Excretion	Mostly fecal
Identifiers
CAS number	192725-17-0 Y
ATC code	J05AR10 (with ritonavir)
PubChem	CID 92727
DrugBank	DB01601
ChemSpider	83706 Y
UNII	2494G1JF75 Y
KEGG	D01425 Y
ChEMBL	CHEMBL729 Y
Chemical data
Formula	C37H48N4O5
Mol. mass	628.810 g/mol
SMILES O=C(N[C@@H](Cc1ccccc1)[C@@H](O)C[C@@H](NC(=O)[C@@H](N2C(=O)NCCC2)C(C)C)Cc3ccccc3)COc4c(cccc4C)C
InChI InChI=1S/C37H48N4O5/c1-25(2)34(41-20-12-19-38-37(41)45)36(44)39-30(21-28-15-7-5-8-16-28)23-32(42)31(22-29-17-9-6-10-18-29)40-33(43)24-46-35-26(3)13-11-14-27(35)4/h5-11,13-18,25,30-32,34,42H,12,19-24H2,1-4H3,(H,38,45)(H,39,44)(H,40,43)/t30-,31-,32-,34-/m0/s1 Y Key:KJHKTHWMRKYKJE-SUGCFTRWSA-N Y
Y (what is this?)  (verify)

Lopinavir (ABT-378) is an antiretroviral of the protease inhibitor class. It is used as a fixed-dose combination with another protease inhibitor, ritonavir, under the trade names Kaletra (high-income countries) and Aluvia (low-income countries).

Pharmacology

Lopinavir is highly bound to plasma proteins (98–99%).

There are contradictory reports regarding lopinavir penetration into the cerebrospinal fluid (CSF). Anecdotal reports state that lopinavir cannot be detected in the CSF; however, a study of paired CSF-plasma samples from 26 patients receiving lopinavir/ritonavir found lopinavir CSF levels above the IC₅₀ in 77% of samples.

Clinical properties

Side effects, interactions and contraindications have only be evaluated in the drug combination lopinavir/ritonavir.

External links

• Abbott: Kaletra (lopinavir/ritonavir) tablets